When I set out to make cookie advent calendars this year, I really did not think it was that big of a deal. The only thing I was thinking about is how good of a gift it would be, since I’m always trying to eat as many holiday cookies as possible, but would much rather prefer a slow ration of them than an all-out-sprint during the last two weeks of December. Plus, acts of service is my love language, so a homemade gift just felt right.

What this project did turn into was 40 hours of work, four trips to UPS, and only one 20-minute spell of sitting on my kitchen floor staring into space. Yet it also turned into the best gift I’ve ever given, and I think everyone should do it at least once.

And going back to my “it’s not that big of a deal” delusion – organization-wise, it really isn’t that crazy of an endeavor. It’s just a cookie box, times two. And yes, it will probably need an entire weekend, but I wanted to use this newsletter to outline my process to hopefully save you a bit of the mania, or just help you make some insane cookie boxes this month.

Choosing recipes and getting started

If you have a bunch of cookbooks on your shelf, I’d suggest starting there. While I love baking from recipes online, having cookie recipes already in print was so supremely helpful. Plus, this gave me a chance to cook new recipes from cookbooks I love.

To keep everything streamlined, I just kept the cookies in book order, so my list ended up looking like this:

1. Peanut Butter Blossoms – COOKIES Page 51
2. Gingerbread Latte Cookies – COOKIES Page 233
3. Best Sugar Cookies – COOKIES Page 249
4. Pecan Squares – COOKIES Page 253
5. Maple Coconut Bars – Zoë Bakes Cookies Page 127
6. Linzer Cookies – Zoë Bakes Cookies Page 109
7. Gingerbread Cookies – Zoë Bakes Cookies Page 103
8. Puff Pastry Wreaths – Ballymaloe Desserts Page 184
9. Cranberry Macaroons – More Than Cake Page 23
10. Coffee Hazelnut Linzers – More Than Cake Page 39
11. Cheeziest Biscotti – Salty Cheesy Herby Crispy Snackable Bakes Page 176
12. Hot Chocolate Cookies – Sweet Tooth Page 244
13. Cinnamon Roll Cookies – Sweet Tooth Page 134
14. Peppermint Kisses – Pastry Love Page 405
15. Vanilla-Mint Marshmallows – Pastry Love Page 408
16. Christopher’s Honeycomb – Pastry Love Page 411
17. Apple Cider Miso Caramels – Pastry Love Page 417
18. Salted Halva Blondies – Dessert Person Page 128
19. Olive’s Famous Brownies – Olive + Gourmando Page 180
20. Olive’s Original Oatmeal Cookies – Olive + Gourmando Page 170
21. Gingerdoodles – JustineSnacks.com
22. Brownest Butter Darkest Chocolate – Justine Cooks Page 226
23. Sticky Toffee Cookies – Recipe coming soon!
24. Eric’s Orange Truffle Brownie – Justine Cooks Page 229

Materials and ingredients

The materials were the biggest pain to source, but once I had everything it was easy to assemble the boxes and put it all together. Here’s everything I used:

• Cookie Boxes
• Advent Number Stickers
• Ribbons
• Cookie Bags
• Tissue Paper for the Caramels

The ingredients were another huge hurdle for calculations. I used a table on Notion to sum up the amount of grams I would need for every item. Having the grams total helped me know exactly how much I needed to get at the store (i.e. a bag of pecans is 227 grams, so I knew I needed at least 2 bags to have the 350 grams I needed for multiple recipes).

Baking and storing

My active baking was only a day and a half, mostly because I wanted the cookies to be as fresh as possible when they were packaged. It felt fast, but you can absolutely do this in a weekend with some pre-planning. My best tips:

• Before you start baking, have your scale in one spot and put a spoon or measuring utensil in each of your “base” ingredients (ie. flour, sugar, brown sugar etc.) This makes it so you can always measure out the base ingredients without needing to dirty another spoon or cup. A spoon lives in my flour container now and it’s my favorite hack.
• Make sure you have 1-2 big open tables ready. These cookies will need a place to land. Prep the tables with cooling racks if you have them, just so you aren’t scrambling for places when it’s finally time.
• Do dishes as you go – using the same bowl over and over again saved my sanity (and my kitchen clutter).
• Use an electric hand mixer, with your stand mixer as the last resort. This saved me so much space but also so much time. A hand mixer let me be a little more nimble when jumping from recipe to recipe. I love my stand mixer but she is a lot to clean and takes up a ton of counter space.
• Do the doughs first and the bakes later – this way your oven won’t have to be on for twelve hours straight. This wasn’t an exact science, but I tried to get as many doughs done and in the fridge as possible before I turned on the oven and started baking.
• When it’s time for the roll-out cookies, do them all at once. That way you only have a chaotic flour-filled counter once 🙂

I know there are a million other tips I could give but then it would feel like a lecture, these are just a few of the things that really saved me time!

Packaging, storing and how they keep for 24 days!

My favorite part was when the cookies were finally ready to be packaged. In the interest of time and organization, I packaged all the cookies and then put them into bowls, each organized by number. That way when I was making the boxes, I could lay out the bowls chronologically and it made boxing super easy.

I scanned all of the recipes from their books into my phone and added them to a PDF I created on Canva. The first page listed all the recipes, and then the recipes followed so that anyone who got the calendar could remake a recipe if they liked one.

And the question I got asked the most: How do these store? 

Which, great question. For freshness, I asked everyone who received a box to freeze them and then pull a cookie out the night before to let it thaw at room temperature. The system is working well, and it turns out the cookies only need a few hours to thaw. So most of my friends have been pulling them out in the morning.

And now, the cookie superlatives

And now! My favorites, the easiest, and the best, and others:

The best overall book for Christmas baking: COOKIES by NYT Cooking

I was not expecting to be as wow-ed by this book as I was, but everything was extremely

delicious. This book had the Gingerbread Latte Cookies that were soft and chewy and truly the only gingerbread I ever want to eat again. The sugar cookie roll-out recipe from this book is also phenomenal. And the pecan bars won another superlative that you’ll see below…

Best for cookies when you need just the classics: Zoë Bakes Cookies

Look, I normally hate gingerbread cookies. But Zoë’s book made me LOVE them. She also has an entire section for holiday baking, and it’s all very classic cookies. A great option for if you want an encyclopedic cookie book!

Best for gluten-free eaters who still want cookies – Gingerdoodles (from this blog!)

So, these are my snickerdoodle recipe, but add ground ginger and a tiny bit of freshly grated ginger to the sugar topping (skip the cinnamon). They are so insanely chewy and delicious that you’d never know they are gluten free cookies.

My sleeper hit: Cheeziest Biscotti from Salty Cheesy Herby Crispy Snackable Bakes

If I told you you could make a cookie that tastes like a giant Cheez-it, would you make it? I hope so because this is it, and I think about them daily.

My personal favorite recipe: Apple Cider Miso Caramels from Pastry Love

Okay, to be fair this is the one recipe I messed up. But when I did it again I realized why all the work is worth it. These are chewy and caramel-y but taste like concentrated apple cider. It’s like eating a caramel apple but sans apple….yet…with apple?

The least work but most impressive: Christopher’s Honeycomb from Pastry Love

I had never made honeycomb before, but it really is just heating up sugar and honey until it’s bubbling, then adding baking soda and pouring it out. It’s so surprisingly easy and fun that I will for sure be making it again. Plus, it keeps forever.

The easiest recipe: Sesame Halva Blondies from Dessert Person

Dessert Person has never really been my book. I find all the recipes a little too strenuous and they always need a small tweak on my end to work for me. But this is why I was so pleasantly surprised that I could make these blondies in one bowl without even thinking too hard. And the result was fudgey and delicious. Will make again.

The “I Cannot Wait to Make These Again”s: Pecan Bars from COOKIES and Oatmeal Cookies from Olive et Gourmando

Both of these recipes will be in my kitchen again before the year is over. The oatmeal cookies are huge and seedy and nutty, while the pecan bars are soft and rich (and also, gorgeous, see photo above).

The one to appease the chocolate lovers: Eric’s Orange Truffle Brownie

Yes, okay, this is from my book. But it comes out tasting like a dense chocolate truffle and I know at least one person in your life is a chocaholic. Make them happy with these <3.

And that’s it for the advent calendar! Feel free to let me know if you have any questions, I’ll try to answer as best as I can 🙂